Was there last month and wanted to give a quick wrap up of the dining. Which was much more expensive than I expected, tho I shouldn't have been too surprised with all the cruise ships coming in.
My favorite place was Cafe Puerto Rico at the edge of Old San Juan by the park. It had a little outdoor dining area but I ate at that bar (was by myself and had asked here about bar/solo dining, not a problem at all) and got a great grilled grouper w/ garlic sauace and rice/beans and plantain chips. Which were basically fries out of plantains, kind of dry but okay. Got one of their fancy cocktails which the bartender was kind enough to give for free at the end of the nite. Good prices with most items about $12-15 and a lot of food for the $$. Went there again my last nite and had good sized shrimp in a creole sauce, rice/beans and sweet plantains. Good basic food, good price, friendly staff.
Ate at the bar at Baru on the happening Calle San Sebastian. This was a "hip" restaurant you'd find in any city but I enjoyed it. Friendly people at the bar, one man gave me half his appetizers: huge shrimp cocktail and a goat cheese dip with fried yucca that was pretty tasty. The seafood risotto at about $18 was good not great. Nice place, fun street with lots of bars.
Went to check out the Ocean Park area where I almost stayed, was very happy with the Sheraton in Old SJ (and their breakfast buffet is quite decent). But made sure to stop at Kasalta Bakery where a flaky meat turnover and flan was cheap and good. Meant to go back to get a sandwich but didn't make it. Also grabbed a good pastry at La Bombonara in town, tons of stuff for just $1. And lunch at the classic Cafeteria Mallorca on Calle San Francisco was a good experience. Got their special sandwich which was basically chicken, ham and egg I think w/ lettuce and tomato served w/ fries ($6.50). Counter service from men who've been working there for years, lots of old Coke accessories, regulars coming in for coffee, cool place.
Lunch at the Parrot Club on Calle Fortaleza wasn't too exciting. Felt the need for a salad and the smoked chicken w/ goat cheese salad ($12) was fine but a little boring. It felt good to be in air conditioning at least.
Had nice tapas at the bar at the El Picoteo in the El Conveneto Hotel. Well, just cod fritters and a sangria but that was filling enough. I wasn't thrilled with the tres leches cake tho and thought it was a little pricey at $8. More nice people working and sitting at the bar. Also stopped at the bar at Cafe Amadeus on San Sebastian where a friend and I got drinks and split some appetizers. Damned if I can't remember them, they were good not great. And the bartender came thru with a mango martini for me which wasn't on the menu. Good thing I wasn't trying to read there, very dark. We then went down the street for dinner at Casa Borenquen where the owners were sweethearts and told us about redoing the building (property ain't cheap there). Great steak that was actually served with green vegetables (!) at about $18 and his crabcake had a spicy kick and was filled with crab for about $10 or $12. One of them was a Patriots fan.
There was an outdoor fair the last nite there were I got a filled fried pastry (can't remember the name) for just a $1, some entertainment and vendors. And the first Tues. of the month has lots of artists out in the squares and galleries open, so remember that if you time it right. A few random showers but the weather was perfect otherwise, fun city.